Tetrahydrofuran → 3-Chloro-2-(trifluoromethyl)phenylacetonitrile

HRID 1749489ノート

反応式

HRID 1749489 の反応式
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]([F:17])([F:16])[F:15])(=O)=O.C[Si](C)(C)[C:20]#[N:21].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(#N)C.O.C(OCC)(=O)C>[Cl:13][C:9]1[C:8]([C:14]([F:17])([F:16])[F:15])=[C:7]([CH2:6][C:20]#[N:21])[CH:12]=[CH:11][CH:10]=1

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 1181621493-Chloro-2-(trifluoromethyl)benzyl methanesulfonate

生成物 1

HCID 1181621683-Chloro-2-(trifluoromethyl)phenylacetonitrile収率 583.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 3-chloro-2-(trifluoromethyl)benzyl methanesulfonate (0.150 g, crude) and trimethylsilanecarbonitrile (119 mg, 1.2 mmol) in acetonitrile (5 mL) was added a solution of tetrabutylammonium fluoride in THF (1M, 1.2 mL, 1.2 mmol). The reaction was stirred at room temperature for 2 h. The reaction was treated with ethyl acetate and water, and the separated organic layer was washed with brine, dried and concentrated to give the crude product, which was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to afford the title compound (0.10 g, 3.03 mmol, 68% yield over three steps) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 7.56-7.48 (m, 3H), 3.99 (d, J=2.0 Hz, 2H).

後処理

  1. washthe separated organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-0c9564ea0347453c81c33ceba4509fde
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

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